Win a Date with Jill

S7 E5: Suit up for our first-ever edition of "Win A Date with Jill." These 24 charming bachelors will do their best to impress our lovely co-host, Jill Wagner, as they showcase their dynamite personalities while tackling the world's toughest obstacle course. The contestants will prove whether or not they are boyfriend material before they face Jill's bodyguard "The Classic Sweeper." Only 1 will be lucky enough to score the cash prize, a solo date with Jill and a spot to compete in the "Tournament of Champions" at the end of the season.